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4-Chloroaniline → N-(4-Chlorophenyl)-2-(quinolin-4-ylmethylthio)pyridine-3-carboxamide

HRID 599362
ノート
印刷プレビュー

反応式

HRID 599362 の反応式
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][S:12][C:13]2[C:18]([C:19]([OH:21])=O)=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:3][CH:2]=1.[Cl:22][C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=1.C(N(CC)C(C)C)(C)C.C(OCC)(=O)C>CN(C)C=O>[Cl:22][C:23]1[CH:29]=[CH:28][C:26]([NH:27][C:19]([C:18]2[C:13]([S:12][CH2:11][C:4]3[C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[N:1]=[CH:2][CH:3]=3)=[N:14][CH:15]=[CH:16][CH:17]=2)=[O:21])=[CH:25][CH:24]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 78124-ChloroanilineHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 670539532-(Quinolin-4-ylmethylthio)pyridine-3-carboxylic acid

生成物 1

HCID 11647134N-(4-Chlorophenyl)-2-(quinolin-4-ylmethylthio)pyridine-3-carboxamide収率 75%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetrauroniumhexafluorophosphate (140 mg, 0.38 mmol) was added to a solution of 2-(quinolin-4-ylmethylthio)pyridine-3-carboxylic acid (Reference Compound No. 7-1.91 mg, 0.31 mmol), 4-chloroaniline (52 mg, 0.40 mmol) and N,N-diisopropylethylamine (0.13 mL, 0.74 mmol) in anhydrous N,N-dimethylformamide (2.0 mL) at room temperature, and the mixture was stirred for 24 hours. Ethyl acetate (50 mL) was added thereto, and the whole was washed with saturated aqueous sodium hydrogencarbonate solution (50 mL, twice) and brine (50 mL), The organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and then the precipitated solid was filtered off and washed with a mixture of diethyl ether and ethyl acetate (1:1). The resulting solid was dried at 50° C. under reduced pressure to give 93 mg of the target compound as a reddish-brown solid (Yield: 75%)

後処理

  1. washthe whole was washed with saturated aqueous sodium hydrogencarbonate solution (50 mL
  2. dry with materialtwice) and brine (50 mL), The organic layer was dried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. filtrationthe precipitated solid was filtered off
  5. washwashed with a mixture of diethyl ether and ethyl acetate (1:1)
  6. customThe resulting solid was dried at 50° C. under reduced pressure

出典と根拠

ORDレコード
ord-3bd7756da98d44058aadb589a1dc0187
出典データセット
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07897774B2

反応ノート

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